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But how do you flirt with a GILF? The first thing to recognize is that she is a generation older than you.

Game that is consistently effective with women your own age is not likely to work with her. In my experience, fifty plus women are easily charmed but not easily impressed.

Bragging and bravado will get you nowhere. However, she will be turned off if you come across as thinking too much of yourself.

Even if in her mind the relationship between you will be purely sexual, she has probably seen enough assholes to know one on sight.

Mature women like subtlety, wit, and graciousness. Make small talk, but show an interest in her life and work. You should also continue to look at her and drop casual compliments to her in ways that demonstrate your physical attraction to her body.

At first she may be a little embarrassed by the attention—especially if she is a more understated beauty—but after a while she will get used to it, and then really begin to enjoy it.

Here are some ways to start a conversation through text or chatting: "Hey, how's it going? Don't talk about yourself too much.

The majority of people are most comfortable talking about themselves because it's a topic they know well. Instead of taking the easy way out and discussing you endlessly, encourage the other person to talk about him or herself.

However, you can and should occasionally throw some personal facts in the person's direction to help them to ask questions about you in turn.

The key is to leave it up to them to pursue an interest in things relevant to yourself. This tactic actually serves two purposes: Not only does it keep the conversation going, but it allows you to find out more about your crush.

You don't have to possess prior information about the other person to do this step. If you don't know him or her very well yet, you can ask: "How did your day go?

For instance, maybe he's really into basketball, or you know she loves to read. Know when to press for more information. You can keep the discussion lively and interesting without probing too deeply on personal topics.

For instance, asking your crush what exactly he or she likes about running cross-country would be a great idea; asking him or her for more details on family relationships or close friendships would be too much, too soon.

You can do it in a joking, flirtatious bantering way that doesn't feel too serious, or like you're interviewing the person.

Here are some ways to ask for more information flirtatiously: "So are you planning on spending all night online or do you have more exciting plans for this evening?

Is that who you spend most of your time with? Compliment your crush early in the conversation. Don't chicken out and skip this step — it might seem difficult, but it's incredibly important.

A compliment communicates that you're potentially interested in dating, and steers you away from the dreaded friend-zone. Here are some basic compliments you could use: If you don't know your crush very well yet, but you're working on it, use a compliment oriented in this direction.

Say something like, "It's so easy to talk to you," or "I kind of can't believe I'm getting to know someone as interesting as you. Be bold. If none of the suggestions above appeal to you, go for broke and pay your crush a bold compliment.

Don't come on too strong. Avoid loading compliments with feelings too early. Leaving a person slightly uncertain of the extent of your feelings for them can increase your attractiveness, giving you a bit of a mysterious edge.

The point is not to make the person question whether you like them at all, but to make them wonder how much you like them.

If you just openly say, "I have a big crush on you" or "I've always thought you were so hot," then you're taking the mystery out of the exchange.

Instead, you can send a text or a message that says something like, "You looked cute in your new sweater today" or another comment that is nice and flirtatious without giving it all away.

Convince your crush to pursue you instead of having to do the work yourself. Though flirting should let the person know that you like him or her, you shouldn't make it seem like you're doing all of the work.

Instead, you should be just flattering enough so that the person knows you're interested, but leave him or her to wonder just how much you care.

To achieve this, try phrasing compliments objectively rather than subjectively. Here are examples of objective vs subjective compliments: "I really like your eyes, they're so pretty.

They tell the person that they've succeeded in winning your heart. This is great if you've already built up a solid relationship, but early on it can make you seem "too easy".

Although technically both sentences are you conveying that you like the person's eyes, this one makes it more of an observation than a personal opinion.

It implies that you find the person attractive but does not confirm it outright. As such, the receiver will feel both flattered and drawn to figure out how much attractive you find them.

Tease gently. Because you can't use body language to communicate over text or chat, you'll have to rely on your words to keep the mood light and fun.

Make it clear that you're kidding. The drawback of using text to communicate is that you can't always read the emotion behind the words. If you're going to flirt with someone by teasing them, make extra sure that you're implying it's a joke.

You can use winking smiley faces, all caps, or exclamation points to communicate this. Just don't overdo it with the emoticons or it'll begin to feel corny for the other person.

If you've already sent something that could be interpreted the wrong way, make your meaning crystal clear.

Say something like " joke " or "jk" to make a quick save. Always leave your crush wanting more. As much as you might want to text this person forever, it's best to bow out before the conversation goes stale as all conversations are bound to do at some point.

The best way to avoid an awkward pause is to leave before one happens. Ending the conversation on a good note will lead your conversational partner to look forward to the next time you can chat.

Set up your next interaction before you go. Throw out something like "Hey, so I'll see you around tomorrow?

It doesn't have to be complicated — a simple "This was awesome" or "I had a good time talking to you" is enough. If you're texting, you can be a bit more casual about it.

Be careful not to over-compliment your crush. Your compliments will have a lot less meaning if you bestow them for every single positive trait the person has.

Instead, reserve them for meaningful things that are important to the person, such as complimenting a skill they take pride in. Don't take it too seriously.

Keep in mind that flirting is supposed to be fun and try not to be crushed if your efforts aren't successful — not every interaction will be a perfect Stay positive, and try again with someone else.

As with anything else, flirting improves with practice. Flirting also doesn't have to have an endgame; not every flirtation ends in a date. Sometimes, you may just want to flirt for the fun of it, instead of hoping it will go somewhere.

Flirting can help you meet new people, feel more comfortable, and learn to mingle. You don't need to put any pressure on yourself to make it mean something or to be perfect.

You can also try complimenting them or making other small gestures to show you care, like surprising them with little gifts.

If you get the sense they might be interested, have an honest conversation about how you feel. Not Helpful 52 Helpful Be friendly and be yourself.

Not Helpful 29 Helpful He does! Hold eye contact with him and wait for him to blush or look away. Not Helpful Helpful Ask him out first! If you insist, you can hint for him to make a move , but if he's shy you might be waiting a long time.

Only give out your phone number to someone you're actually interested in. If someone seems sleazy or won't stop asking you, we have some ideas for you.

Put your hand on his arm and look into his eyes. It's less fun, but it gets you where you want to be.

Include your email address to get a message when this question is answered. By using this service, some information may be shared with YouTube.

Otherwise, you risk accidentally leading them on, which can lead to an embarrassing moment and uncomfortable interactions afterward.

Helpful 23 Not Helpful 4. Let go of any neediness you might have. Neediness is a precursor to obsessiveness, and obsessiveness is creepy. Needy people are imbalanced and unstable people because their happiness hinges too greatly on someone else, rather than a stable sense of self-worth.

If you're projecting a vibe that you'll be devastated if a person doesn't want to be your friend or romantic partner, the lightheartedness that makes flirting fun will be extinguished.

Helpful 14 Not Helpful 2. If you're flirting with a girl and thinking about breaking the touch barrier, test the waters with impeccable manners. You can do this whether you're with a bunch of other people or if it's just the two of you.

It may seem a little juvenile because you used this tactic when you were 12 and too shy to tell a girl you liked her.

But the fact that this move is so junior high is why it's so charming — not only are you telling her something sweet, but you're doing it in a way that shows you still think she's way cooler than you just like that pretty popular girl.

Before you were dating, there was so much sexual tension, which made flirting work. Build that tension again by making her wait for it.

Don't kiss her, just stare at her mouth. Hold on to the anticipation of the kiss. There is nothing hotter than a genuine compliment.

Now that you're married, you know the most intimate things about her, so you can compliment her on something only you know about her. When you were dating, you probably spent a good amount of time combing your hair so you looked your best.

Now that you're married, you actually have an advantage because you know what she thinks is hot.

Whether she goes gaga for guys in cardigans, or suits are her thing, you know what she likes. Wear that. Touch is the classic flirting move.

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